Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | HCID 18790579 | HCID 18790579 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 18790540 | HCID 18790540 | 36.5% |
Reaction Steps
4-[2-(2-Naphtyl)-2-oxoethylthio]quinoline (Compound 2; 450 mg, 1.37 mmol) was dissolved in ethanol (50 ml), added at -15° C. with sodium borohydride (70 mg, 3.04 mmol), and stirred at -15° C. for two hours. The reaction mixture was added with water and neutralized by 2N hydrochloric acid. The solvent was removed under reduced pressure. The residue was extracted with ethyl acetate, washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed by silica gel column chromatography (hexane:ethyl acetate=1:4) to obtain 165.7 mg of the titled compound (36.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06057447 |
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| Source dataset | uspto-grants-2000_05 |
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| ORD ID | ord-85a42bac711e4b0d89192a55405d0747 |
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| Source note | uspto-grants-2000_05 |
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